| OPRF V Hinsdale Central and Lyons Townshp | 09/02/2021 | Hinsdale, IL | Hinsdale Central High School - Katherine Legge Memorial Park |
| Fenton Earlybird Invitational | 09/04/2021 | Bensenville, IL | Fenton (IL) High School - Fenton HS |
| OPRF V Glenbard West | 09/13/2021 | Schiller Park, IL | Oak Park-River Forest HS - Schiller Woods |
| Richard Spring Invitational | 09/18/2021 | Peoria, IL | - Detweiller Park |
| Downers Grove North v York v Oak Park-River Forest | 09/23/2021 | Woodridge, IL | Downers Grove North HS - Green Valley Forest Preserve |
| Palatine Invite - Meet of Champions | 09/25/2021 | Palatine, IL | Palatine High School - Deer Grove East Forest Preserve |
| OPRF V Proviso West | 09/30/2021 | Hillside, IL | Proviso West High School - Campus XC Course |
| New Balance/Naperville Running Co. Twilight Invite | 10/06/2021 | Naperville, IL | Naperville North High School - Cross Country Course |
| West Suburban Conference - Silver Division | 10/16/2021 | Western Springs, IL | Lyons Township High School - South Campus |
| Buffalo Grove Race Car Invite F/S | 10/19/2021 | , | - |
| IHSA 3A Boys Cross Country Regionals | 10/23/2021 | Western Springs, IL | Lyons Township High School - Lyons Twp HS - South Campus Bennett Field |
| IHSA Sectional Championships | 10/30/2021 | TBA, IL | IHSA - TBA |
| IHSA Boys 3A Cross Cross Country State Championship | 11/06/2021 | Peoria, IL | - Detweiller Park |
